Jean-Marie Ferland

Photolabile p-methoxyphenacyloxycarbonyl group for the protection of amines

Abstract P-Methoxyphenacyloxycarbonyl (Phenoc) is a new photolabile protective group for amines. Various phenacyl urethanes, i.e. Phenoc protected amines, have been prepared. An application of the group in peptide synthesis is reported.

Herpes simplex virus ribonucleotide reductase subunit association inhibitors: the effect and conformation of β-alkylated aspartic acid derivatives

Incorporating beta-alkylated aspartic acid derivatives into herpes simplex virus ribonucleotide reductase subunit association inhibitors can improve inhibitor potency up to 50 times over the corresponding inhibitors containing an unsubstituted aspartic acid. A combination of NMR studies, conformational analysis, and molecular mechanics calculations suggests that the beta-alkyl group improves inhibitor potency by favoring the bioactive conformation of the critical aspartic acid carboxyl group. Further support for this hypothesis is provided by a potent conformationally restricted aspartic acid derivative in which the carboxyl group is locked in the putative bioactive conformation.